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Bromodiphenhydramine

Bromodiphenhydramine structure

CAS No:
118-23-0
Formula:
C17H20BrNO
Chemical Name:
Bromodiphenhydramine
Synonyms:
Ethanamine,2-[(4-bromophenyl)phenylmethoxy]-N,N-dimethyl-;Ethylamine,2-[(p-bromo-α-phenylbenzyl)oxy]-N,N-dimethyl-;2-[(4-Bromophenyl)phenylmethoxy]-N,N-dimethylethanamine;Ambodryl;Bromazin base;Bromo-Benadryl base;β-(p-Bromobenzhydryloxy)ethyldimethylamine;Bromodiphenhydramine;2-(p-Bromo-α-phenylbenzyloxy)-N,N-dimethylethylamine;Deserol base;Bromazine;Bromdiphenhydramine;Bromanautine;Histabromamine;Bromo-Benadryl;Deserol;Neo-Benadryl;4-Bromodiphenhydramine
Categories:
Active Pharmaceutical Ingredients > Antiallergic Drugs

Description

ChEBI: A tertiary amino compound that is the 4-bromobenzhydryl ether of 2-(dimethylamino)ethanol. An antihistamine with antimicrobial properties, it is used in the control of cutaneous allergies.

Solid

Bromazine is a tertiary amino compound that is the 4-bromobenzhydryl ether of 2-(dimethylamino)ethanol. An antihistamine with antimicrobial properties, it is used in the control of cutaneous allergies. It has a role as an antimicrobial agent, a muscarinic antagonist and a H1-receptor antagonist. It is a tertiary amino compound and an organobromine compound. It contains a bromazine hydrochloride.|Bromodiphenhydramine is an ethanolamine antihistamine with antimicrobial property. Bromodiphenhydramine is used in the control of cutaneous allergies. Ethanolamine antihistamines produce marked sedation in most patients.

Bromodiphenhydramine Basic Attributes

Molecular Weight：

107.9174

Exact Mass：

334.25

EC Number：

204-238-8

DSSTox ID：

DTXSID6022688

ATC Code：

R - Respiratory system

HScode：

2922199090

Characteristics

PSA：

12.47000

XLogP3：

4.11670

Appearance：

Solid

Density：

1.259g/cm3

Boiling Point：

151-154 °C @ Press: 0.3 Torr

Flash Point：

194.1ºC

Water Solubility：

3.45e-03 g/L

Toxicity

Toxicity Summary：

Signs of overdose include wheezing, tightness in the chest, fever, itching, bad cough, blue skin color, fits, swelling of face, lips, tongue, or throat.

Protein Binding：

96%

Drug Information

Drug Indication：

For management of symptoms related to hay fever and other types of allergy and used to help bring up phlegm, thin secretions, and make a cough productive.

Pharmacology：

Bromodiphenhydramine is an antihistamine of the ethanolamine class. Ethanolamine antihistamines have significant antimuscarinic activity and produce marked sedation in most patients. In addition to the usual allergic symptoms, the drug also treats irritant cough and nausea, vomiting, and vertigo associated with motion sickness. It also is used commonly to treat drug-induced extrapyramidal symptoms as well as to treat mild cases of Parkinson's disease. Rather than preventing the release of histamine, as do cromolyn and nedocromil, Bromodiphenhydramine competes with free histamine for binding at HA-receptor sites. Bromodiphenhydramine competitively antagonizes the effects of histamine on HA-receptors in the GI tract, uterus, large blood vessels, and bronchial muscle. Ethanolamine derivatives have greater anticholinergic activity than do other antihistamines, which probably accounts for the antidyskinetic action of Bromodiphenhydramine. This anticholinergic action appears to be due to a central antimuscarinic effect, which also may be responsible for its antiemetic effects, although the exact mechanism is unknown.

Absorption：

Well absorbed in the digestive tract.

Metabolism/Metabolites：

Hepatic (cytochrome P-450 system); some renal.

Biological Half-Life：

1 to 4 hours

Mechanism of Action：

Bromodiphenhydramine competes with free histamine for binding at HA-receptor sites. This antagonizes the effects of histamine on HA-receptors, leading to a reduction of the negative symptoms brought on by histamine HA-receptor binding.

MeSH Entry Terms：

ambodryl

Bromodiphenhydramine Use and Manufacturing

Uses

Antihistaminic.

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals

Computed Properties

Molecular Weight:334.2
XLogP3:4
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:6
Exact Mass:333.07283
Monoisotopic Mass:333.07283
Topological Polar Surface Area:12.5
Heavy Atom Count:20
Complexity:258
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes